A challenging period was ahead for NWS forecasters situated in Oxnard, California in early November 2018 as a strong Santa Ana wind event was forecast to hit the area. Very little rainfall occurred in the months leading up to this event contributed to very dry vegetation across the foothill and mountain areas of southern California. Dry fuels combined with an extremely dry air mass and strong Santa Ana winds brought the fire danger parameters to near 30-year highs. The Woolsey and Hill fires erupted during the afternoon hours on November 8, 2018 in an area just northwest of Los Angeles in the Santa Monica Mountains. The most destructive fire of the two, the Woolsey fire burned over 96,000 acres, destroyed 1,643 structures and damaged 364 others for a total of $6 billion in property loss. The fire also shut down two major highways near the Ventura-Los Angeles County border, hampering evacuation efforts and emergency response. The study presented will focus on the weather conditions leading up to and during the Woolsey and Hill fire starts and comparing surface wind and relative humidity observations to different mesoscale model simulations using different resolutions and parameterizations. The results will help show why certain parameterizations and model configurations are able to resolve the details of these fire weather events in southern California - configurations which can ultimately help in shaping the operational models used by the NWS to provide accurate and timely decision support services to its partners needed to protect their communities.